Silver versus gold catalysis in tandem reactions of carbonyl functions onto alkynes: a versatile access to furoquinoline and pyranoquinoline cores.
An efficient and versatile tandem process of AuI and AgI-catalyzed acetalization and cycloisomerization of 1-alkynyl-2-carbonyl-quinoline substrates has been developed. Silver(I) catalysis has been extensively studied on a broad range of quinoline derivs., e.g. I, leading to a variety of furoquinolines and pyranoquinolines, e.g. II and III. An insight is given for the presumed mechanism along with DFT-B3LYP/6-31G** calcns. to address the 6-endo and 5-exo regioselectivities obsd. [on SciFinder(R)]
Références
- Titre
- Silver versus gold catalysis in tandem reactions of carbonyl functions onto alkynes: a versatile access to furoquinoline and pyranoquinoline cores.
- Type de publication
- Article de revue
- Année de publication
- 2007
- Auteurs
- Godet, Thomas, Vaxelaire Carine, Michel Carine, Milet Anne, and Belmont Philippe.
- Revue
- Chem. - A Eur. J.
- Volume
- 13
- Pagination
- 5632–5641, S5632/1–S5632/46
- ISSN
- 0947-6539
Soumis le 12 avril 2018